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Biological activity of optically pure C-1 altered abscisic acid analogs in Brassica napus microspore embryos

Hays, D.B., Rose, P., Abrams, S.R., Moloney, M.M.
Journal of plant growth regulation 1996 v.15 no.1 pp. 5-11
messenger RNA, germination, dose response, embryo (plant), aldehydes, isomers, gene expression, genes, esters, Brassica napus, mutants, abscisic acid, molecular conformation, alcohols
We have examined the effects of stereochemically pure analogs of abscisic acid (ABA) on three responses in Brassica napus microspore embryos. The analogs used include modifications to natural (S-) (+)-ABA (=N-ABA) at the C-1 and C-1' positions. At the C-1 position, the carboxylic acid function was replaced with an alcohol, aldehyde, or methyl ester functional group, and at the chiral C-1' position both enantiomers were prepared. The rationale for choosing these particular analogs was that they had previously shown some potential as slow release forms of ABA (Gusta LV, Ewan B, Reaney MJT, Abrams SR (1992) Can J Bot. 70:1550-1555). The responsiveness of microspore-derived embryos of B. napus to these analogs was investigated. Three types of responses were evaluated: (1) the inhibition of precocious germination; (2) induction of oleosin gene expression; and (3) induction of napin gene expression. All of the structural analogs of ABA tested were effective in the three assays, regardless of functional group substitution or stereochemistry. However, the three assays showed differential sensitivity to the various analogs. The U-forms of abscisyl alcohol and abscisyl aldehyde were very effective in inhibiting precocious germination (greater than natural ABA). Oleosin mRNA accumulation responded most effectively to U-abscisyl alcohol, while the N-abscisyl aldehyde and ABA methyl ester were the most effective at inducing napin mRNA accumulation. This work highlights the distinct differences in activity which result from using stereochemically pure analogs. In addition, surprisingly potent responses are reported in one or more of the assays for abscisyl aldehyde and abscisyl alcohol.